A Solution to Chemical Pseudaminylation via Development of a Bimodal Glycosyl Donor to Enable Highly Stereocontrolled α- and β-Glycosylation
semanticscholar(2019)
Abstract
Bacterial pseudaminic acids (Pse)
are present on the surface of many pathogenic
bacteria. Herein, we report a robust methodology for the stereocontrolled
chemical glycosylation of
pseudaminic acid to afford both α- (axial) and β- (equatorial) glycosides reliably
with complete stereoselectivity, using a common glycosyl donor (7N-Cbz/5N-azido Pse thioglycoside) simply by changing the reaction
conditions (DCM-DMF, -40 oC and
DCM/MeCN, -78 oC, respectively). Examples of such bimodal
selectivity are both sparse and highly sought-after in carbohydrate chemistry.
This method enables efficient access to pseudaminylated molecules, which will
open up various opportunities in chemical glycobiology research of bacterial
pseudaminic acids and carbohydrate-based antibacterial vaccine development.
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